(3-(Methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indol-6-yl)(piperazin-1-yl)methanone → (1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(piperazin-1-yl)methanone

HRID 630451Notes

Reaction equation

HRID 630451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)=[O:24])[CH:21]=3)[C:16]([S:38]([CH3:40])=[O:39])=[CH:15]2)=[N:12][CH:13]=1.CS(C1C2C(=CC(C(N3CCNCC3)=O)=CC=2)N(C2N=CC(C3C=CC=CC=3)=CN=2)C=1)=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[N:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:24])[CH:21]=3)[C:16]([S:38]([CH3:40])=[O:39])=[CH:15]2)=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 118666184(3-(Methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indol-6-yl)(piperazin-1-yl)methanoneHCID 131735392tert-Butyl 4-(1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carbonyl)piperazine-1-carboxylate

Product 1

HCID 118671941(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(piperazin-1-yl)methanone

Procedure

Prepared from 13c) (170 mg, 0.30 mmol, 1.0 eq) in analogy to the procedure of 12e). White solid. Yield: 130 mg (71% of theory). Melting range: 199-203° C. HPLC (method 3): Rt=4.04 min. Mass spectroscopy: m/z: [M+H]+=464.1.

Sources & evidence

ORD record
ord-93311710b5a4444d90809ecc2d21ec1a
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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